M mag7ical Full Member 10+ Year Member Joined Jan 20, 2009 Messages 105 Reaction score 0 Points 0 Pre-Dental Jun 30, 2010 #1 Advertisement - Members don't see this ad Q. How would you convert a benzyl alcohol into an aniline? A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2 Can someone walk me through each step? I'm unable to follow.
Advertisement - Members don't see this ad Q. How would you convert a benzyl alcohol into an aniline? A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2 Can someone walk me through each step? I'm unable to follow.
R RCT PC CRN RCT-PC-CRN 10+ Year Member Joined May 12, 2009 Messages 220 Reaction score 0 Points 1 Jun 30, 2010 #2 mag7ical said: Q. How would you convert a benzyl alcohol into an aniline? A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2 Can someone walk me through each step? I'm unable to follow. Click to expand... Step 1. Oxidation to -COOH using KMnO4 Step 2. Nu substitution using NH3 to yield Amide Step 3. Hoffman rearrangement using Br2/OH - gives you Aniline and CO2 Hope this help Upvote 0 Downvote
mag7ical said: Q. How would you convert a benzyl alcohol into an aniline? A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2 Can someone walk me through each step? I'm unable to follow. Click to expand... Step 1. Oxidation to -COOH using KMnO4 Step 2. Nu substitution using NH3 to yield Amide Step 3. Hoffman rearrangement using Br2/OH - gives you Aniline and CO2 Hope this help
U UndergradGuy7 Full Member 15+ Year Member Joined Jun 24, 2007 Messages 897 Reaction score 2 Points 4,571 Pre-Dental Jun 30, 2010 #3 mag7ical said: Q. How would you convert a benzyl alcohol into an aniline? A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2 Can someone walk me through each step? I'm unable to follow. Click to expand... KMnO4 makes CH2OH into a carboxylic acid. NH3 + carboxylic acid makes C=O(OH) into C=O(NH2) an amide. OBr- is the Hoffman rearrangement I think. It makes you lose the C=O group. So its just phenyl-NH2 Upvote 0 Downvote
mag7ical said: Q. How would you convert a benzyl alcohol into an aniline? A. PhCH2OH -> KMnO4 -> NH3 -> OBr- -> PhNH2 Can someone walk me through each step? I'm unable to follow. Click to expand... KMnO4 makes CH2OH into a carboxylic acid. NH3 + carboxylic acid makes C=O(OH) into C=O(NH2) an amide. OBr- is the Hoffman rearrangement I think. It makes you lose the C=O group. So its just phenyl-NH2
